反応 #92124

反応方程式

1-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]imidazolidin-4-one

sodium hydride

1,1,1-trifluoro-3-iodopropane

→

1-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]-3-(3,3,3-trifluoropropyl)imidazolidin-4-one

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   その他Into a 50-mL 3-necked round-bottom flask purged
2. 2
   温度maintained with an inert atmosphere of nitrogen
3. 3
   その他to react
4. 4
   workup.STIRRINGwith stirring, for an additional 4 days at 30° C
5. 5
   その他The reaction was then quenched by the addition of 10 ml of water
6. 6
   抽出The resulting solution was extracted with 3×10 ml of ethyl acetate
7. 7
   洗浄The resulting mixture was washed with 3×20 mL of brine
8. 8
   濃縮The resulting mixture was concentrated under vacuum
9. 9
   その他This resulted in 10.9 mg (4%) of 1-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]-3-(3,3,3-trifluoropropyl)imidazolidin-4-one as a light yellow semi solid

実験手順

Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 1-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]imidazolidin-4-one (200 mg, 0.38 mmol, 1.00 equiv), N,N-dimethylformamide (5 mL). This was followed by the addition of sodium hydride (46 mg, 1.15 mmol, 3.00 equiv, 60%), in portions at 0° C. The resulting solution was stirred for 30 min at 0° C. To this was added 1,1,1-trifluoro-3-iodopropane (863 mg, 3.85 mmol, 10.00 equiv). The resulting solution was allowed to react, with stirring, for an additional 4 days at 30° C. The reaction was then quenched by the addition of 10 ml of water. The resulting solution was extracted with 3×10 ml of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×20 mL of brine. The resulting mixture was concentrated under vacuum. The residue was applied onto a TLC plate with EA/PE (5:1). This resulted in 10.9 mg (4%) of 1-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]-3-(3,3,3-trifluoropropyl)imidazolidin-4-one as a light yellow semi solid. (ES, m/z): [M+H]+ 616; 1H NMR (300 MHz, CDCl3) δ: 7.97 (s, 1H), 7.88 (d, J=6.0 Hz, 2H), 7.69-7.71 (m, 2H), 7.43 (d, J=7.8 Hz, 1H), 5.12 (s, 1H), 4.69 (s, 1H), 4.05-4.39 (m, 3H), 3.87 (s, 1H), 3.70 (t, J=7.2 Hz, 1H), 3.56 (t, J=7.2 Hz, 1H), 2.46-2.65 (m, 3H), 2.39 (s, 3H).

出典